| Record Information |
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| Version | 5.0 |
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| Status | Expected but not Quantified |
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| Creation Date | 2012-09-11 21:36:03 UTC |
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| Update Date | 2022-03-07 02:54:56 UTC |
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| HMDB ID | HMDB0036459 |
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| Secondary Accession Numbers | |
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| Metabolite Identification |
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| Common Name | Macelignan |
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| Description | Macelignan belongs to the class of organic compounds known as dibenzylbutane lignans. These are lignan compounds containing a 2,3-dibenzylbutane moiety. Macelignan has been detected, but not quantified in, herbs and spices. This could make macelignan a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Macelignan. |
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| Structure | COC1=C(O)C=CC(CC(C)C(C)CC2=CC3=C(OCO3)C=C2)=C1 InChI=1S/C20H24O4/c1-13(8-15-4-6-17(21)19(10-15)22-3)14(2)9-16-5-7-18-20(11-16)24-12-23-18/h4-7,10-11,13-14,21H,8-9,12H2,1-3H3 |
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| Synonyms | | Value | Source |
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| Anwulignan | HMDB | | Calophyn | HMDB |
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| Chemical Formula | C20H24O4 |
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| Average Molecular Weight | 328.4022 |
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| Monoisotopic Molecular Weight | 328.167459256 |
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| IUPAC Name | 4-[3-(2H-1,3-benzodioxol-5-ylmethyl)-2-methylbutyl]-2-methoxyphenol |
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| Traditional Name | macelignan |
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| CAS Registry Number | 107534-93-0 |
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| SMILES | COC1=C(O)C=CC(CC(C)C(C)CC2=CC3=C(OCO3)C=C2)=C1 |
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| InChI Identifier | InChI=1S/C20H24O4/c1-13(8-15-4-6-17(21)19(10-15)22-3)14(2)9-16-5-7-18-20(11-16)24-12-23-18/h4-7,10-11,13-14,21H,8-9,12H2,1-3H3 |
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| InChI Key | QDDILOVMGWUNGD-UHFFFAOYSA-N |
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| Chemical Taxonomy |
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| Description | Belongs to the class of organic compounds known as dibenzylbutane lignans. These are lignan compounds containing a 2,3-dibenzylbutane moiety. |
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| Kingdom | Organic compounds |
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| Super Class | Lignans, neolignans and related compounds |
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| Class | Dibenzylbutane lignans |
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| Sub Class | Not Available |
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| Direct Parent | Dibenzylbutane lignans |
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| Alternative Parents | |
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| Substituents | - Dibenzylbutane lignan skeleton
- Methoxyphenol
- Benzodioxole
- Phenylpropane
- Anisole
- Phenoxy compound
- Phenol ether
- Methoxybenzene
- Phenol
- 1-hydroxy-2-unsubstituted benzenoid
- Alkyl aryl ether
- Monocyclic benzene moiety
- Benzenoid
- Acetal
- Ether
- Organoheterocyclic compound
- Oxacycle
- Hydrocarbon derivative
- Organooxygen compound
- Organic oxygen compound
- Aromatic heteropolycyclic compound
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| Molecular Framework | Aromatic heteropolycyclic compounds |
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| External Descriptors | Not Available |
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| Ontology |
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| Physiological effect | Not Available |
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| Disposition | |
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| Process | Not Available |
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| Role | |
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| Physical Properties |
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| State | Solid |
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| Experimental Molecular Properties | |
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| Experimental Chromatographic Properties | Not Available |
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| Predicted Molecular Properties | |
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| Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Retention Times Underivatized| Chromatographic Method | Retention Time | Reference |
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| Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022. | 8.54 minutes | 32390414 | | Predicted by Siyang on May 30, 2022 | 19.0921 minutes | 33406817 | | Predicted by Siyang using ReTip algorithm on June 8, 2022 | 0.9 minutes | 32390414 | | AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid | 30.0 seconds | 40023050 | | Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid | 2744.9 seconds | 40023050 | | Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid | 541.2 seconds | 40023050 | | Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid | 230.9 seconds | 40023050 | | Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid | 257.5 seconds | 40023050 | | RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid | 359.2 seconds | 40023050 | | Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid | 1008.0 seconds | 40023050 | | BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid | 889.8 seconds | 40023050 | | HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate) | 95.0 seconds | 40023050 | | UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid | 1804.6 seconds | 40023050 | | BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid | 717.1 seconds | 40023050 | | UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid | 1879.7 seconds | 40023050 | | SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid | 559.3 seconds | 40023050 | | RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid | 529.9 seconds | 40023050 | | MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate | 350.0 seconds | 40023050 | | KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA | 362.2 seconds | 40023050 | | Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water | 8.1 seconds | 40023050 |
Predicted Kovats Retention IndicesUnderivatizedDerivatized |
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| GC-MS Spectra| Spectrum Type | Description | Splash Key | Deposition Date | Source | View |
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| Predicted GC-MS | Predicted GC-MS Spectrum - Macelignan GC-MS (Non-derivatized) - 70eV, Positive | splash10-01p9-0901000000-22bfca8f123cc67d052f | 2017-09-01 | Wishart Lab | View Spectrum | | Predicted GC-MS | Predicted GC-MS Spectrum - Macelignan GC-MS (1 TMS) - 70eV, Positive | splash10-000i-1955000000-db8e56fb66b08c29ae2c | 2017-10-06 | Wishart Lab | View Spectrum | | Predicted GC-MS | Predicted GC-MS Spectrum - Macelignan GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum |
MS/MS Spectra| Spectrum Type | Description | Splash Key | Deposition Date | Source | View |
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| Experimental LC-MS/MS | LC-MS/MS Spectrum - Macelignan , positive-QTOF | splash10-000i-0900000000-d8bdc4c1e4a630ae1fe4 | 2017-09-14 | HMDB team, MONA | View Spectrum | | Experimental LC-MS/MS | LC-MS/MS Spectrum - Macelignan , positive-QTOF | splash10-000i-0910000000-c90b1f74544adb5ae68d | 2017-09-14 | HMDB team, MONA | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Macelignan 10V, Positive-QTOF | splash10-004i-0329000000-956206a54fffd039a221 | 2016-08-01 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Macelignan 20V, Positive-QTOF | splash10-08ic-1942000000-026059a678a1532f8b12 | 2016-08-01 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Macelignan 40V, Positive-QTOF | splash10-0i09-5921000000-e058d00c237d34bd5363 | 2016-08-01 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Macelignan 10V, Negative-QTOF | splash10-004i-0009000000-600c1a450b0ced22ebc2 | 2016-08-03 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Macelignan 20V, Negative-QTOF | splash10-004i-0039000000-7002ffddbbdf0a7f195c | 2016-08-03 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Macelignan 40V, Negative-QTOF | splash10-0bu0-1392000000-0f40cab6ee1e5be055f4 | 2016-08-03 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Macelignan 10V, Negative-QTOF | splash10-004i-0009000000-fd417bc7f7b273e09154 | 2021-09-22 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Macelignan 20V, Negative-QTOF | splash10-004i-0169000000-751be5e231bc8180cb86 | 2021-09-22 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Macelignan 40V, Negative-QTOF | splash10-004i-0549000000-d0aaa2726ea7c14d5c05 | 2021-09-22 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Macelignan 10V, Positive-QTOF | splash10-004j-0296000000-78591524d90c87ba316b | 2021-09-22 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Macelignan 20V, Positive-QTOF | splash10-052u-0941000000-dccc0af62bd2f1f9ee0a | 2021-09-22 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Macelignan 40V, Positive-QTOF | splash10-0570-0972000000-b1112c488d3d6031c069 | 2021-09-22 | Wishart Lab | View Spectrum |
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| General References | - Sohn JH, Han KL, Kim JH, Rukayadi Y, Hwang JK: Protective Effects of macelignan on cisplatin-induced hepatotoxicity is associated with JNK activation. Biol Pharm Bull. 2008 Feb;31(2):273-7. [PubMed:18239286 ]
- Ma J, Hwang YK, Cho WH, Han SH, Hwang JK, Han JS: Macelignan attenuates activations of mitogen-activated protein kinases and nuclear factor kappa B induced by lipopolysaccharide in microglial cells. Biol Pharm Bull. 2009 Jun;32(6):1085-90. [PubMed:19483320 ]
- (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
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